ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside
• CAS No.: 1431081-25-2
• Molecular Formula: C₅₈H₆₄O₁₇S
• Molecular Weight: 1065.2
• Mol file: 1431081-25-2.mol

Synonyms:ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside

There total 11 articles about ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-O-benzyl-3,5-di-O-(methoxymethyl)gallic acid (1034343-24-2) + ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside (152964-70-0) → ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside (1431081-25-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 14.5h; Inert atmosphere;

DOI:10.1021/jo4003135

Reference yield:

benzyl bromide (100-39-0) → ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside (1431081-25-2)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium hydrogencarbonate; potassium iodide / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere

3: lithium hydroxide; water / methanol; tetrahydrofuran / 2 h / Reflux

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 14.5 h / 20 °C / Inert atmosphere

With dmap; water; sodium hydride; potassium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium iodide; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil; 4: |Steglich Esterification;

DOI:10.1021/jo4003135

Reference yield:

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8) → ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside (1431081-25-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C / Inert atmosphere

2: hydrogenchloride / water; acetone / 1 h / Reflux

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 14.5 h / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil; 3: |Steglich Esterification;

DOI:10.1021/jo4003135

upstream raw materials:

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

4-O-benzyl-3,5-di-O-(methoxymethyl)gallic acid

ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzylgalloyl)-1-thio-β-D-glucopyranoside